Trust & Will is hiring a

Project Manager (Remote- USA)

San Diego, United States
Hi, we’re Trust & Will. We’re making estate planning simple, affordable, and accessible with a design-first approach and amazing customer support. Since launching in 2017, we have served hundreds of thousands of happy customers nationwide using our complete suite of estate planning services. We’re backed by some of the leading names in venture capital who all believe in our mission to provide families a better way to plan for the future. 

The Ideal Candidate:

Our ideal candidate is a mission-driven, organized, and resourceful individual who will drive the successful delivery of strategic projects here at Trust & Will. The Project Manager in this role is a self-starter with leadership qualities who can work in a fast-paced environment and is comfortable working autonomously. You need to be an excellent communicator who thrives on connecting people, facilitating excellent communication, and building project plans that drive results.

You’ll also be detail oriented & scrappy- if they get thrown a curveball, you know what you’re doing next. You’re emotionally intelligent, have demonstrated experience driving results & outcomes,  and are excited at the opportunity to run multiple projects at a time without missing a beat or compromising the details. 

What you’ll do:

You’ll work closely across all functions at the organization to create project plans, lead day to day progress of tasks, and coordinate cross functional projects while driving teams to meet commitments based on the plans you’ve outlined. 


  • Manage the overall project lifecycle from initiation through successful delivery for various strategic initiatives, from new product launches to internal process improvements 
  • Coordinate with cross functional stakeholders and subject matter experts to ensure quality of project goals & requirements that align with business objectives
  • Develop organized project plans with established timelines that align cross functional stakeholders on responsibilities & deadlines 
  • Gather data from teams to proactively raise prioritization, navigate tradeoffs and escalate issues as needed across the multiple projects you’ll be managing
  • Facilitate meetings, create agendas, document meeting minutes, and track action items
  • Drive cross team collaboration and remove blockers to project success
  • Perform risk analysis & develop contingency plans for any potential project impediments
  • Track project changes and their impact on the cost/timeframe of project delivery
  • Communicate project progress, deliverables, milestones, risks, and dependencies on an ongoing basis
  • Track project changes and their impact on the cost/timeframe of project delivery
  • Ensure quality control of deliverables & milestones prepared by project teams 
  • Facilitate a smooth handoff process from project team to maintenance teams with appropriate controls, monitoring, and documentation
  • Define and create any missing project management processes to help improve operational efficiencies, including but not limited to holding project retrospectives at the completion of each project 

We’d love to hear from you if you meet the below requirements:

  • Experienced: you have 5+ years relevant experience, ideally in a startup & remote environment, and have proven that you are seasoned at managing multiple complex projects simultaneously
  • Detailed & organized: you exhibit superior project timeline development and management skills
  • Expert Written & Verbal Communicator: you have a thoughtful & sensitive approach to communication, are able to influence stakeholders to take action, and can clearly communicate complex information to guide decisions
  • Curious & Quick to Learn: you exhibit a willingness to treat every day like day 1, and can quickly absorb the nuances of complex project requirements & solutions 
  • Team Leader: while you can and will roll up your sleeves to work independently on tasks within a project team when needed, you feel extremely comfortable in delegating tasks to the appropriate stakeholders and holding them accountable for meeting their commitments
  • Comfortable with uncertainty and ambiguity: we are a startup. The future isn’t clear and you are excited to create it. Things change and that’s ok. You are flexible, have the ability to change priorities quickly, and guide others through those changes
  • High Energy and Optimistic: you see challenges as opportunities and are excited to tackle them 
  • Proven Ability to Drive Results: you know that the most critical part of a project is having clear goals and success metrics, and you have a proven track record of creating the necessary controls & reports to monitor success 

Nice To Haves:

  • PMP or CAPM certification
  • Experience in SaaS or similar high growth industries
  • Experience managing projects in Clickup, Jira, Confluence and similar tools 
  • A solid grasp of the software development lifecycle

Benefits & Perks:

  • Join an Inc. Magazine Best Workplace of 2021 winner! 
  • Flexible and unlimited time off including monthly Friends & Family days
  • Medical, dental, and vision
  • Employee sponsored 401k
  • Friday team lunches (when in office)
  • Great work environment (all the time!)
  • Work alongside the founding team and help shape the future of the company
  • $500 WFH Stipend & new Mac 
  • Formal mentorship program

All interviews will be conducted remotely. All new and existing Trust & Willers will continue to work remotely as a remote-first team.


Ensuring a diverse and inclusive workplace where we learn from each other is core to Trust & Will's values. We welcome people of different backgrounds, experiences, abilities, and perspectives. We are an equal opportunity employer and a pleasant and supportive place to work.